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The Preparation of α‐Alkylidene‐γ‐Butyrolactones Using a Telescoped Intramolecular Michael/Olefination (TIMO) Sequence: Synthesis of (+)‐Paeonilactone B
Author(s) -
Edwards Michael G.,
Kenworthy Martin N.,
Kitson Russell R. A.,
Perry Alexis,
Scott Mark S.,
Whitwood Adrian C.,
Taylor Richard J. K.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800558
Subject(s) - intramolecular force , chemistry , sequence (biology) , michael reaction , stereochemistry , natural product , organic chemistry , catalysis , biochemistry
A novel telescoped intramolecular Michael addition/proton transfer/HWE olefination sequence has been developed to provide rapid access to α‐alkylidene‐γ‐butyrolactones. This methodology has been applied to prepare a range of tetrahydrobenzofuran‐2,5‐diones, and related systems, and also utilised in an extremely short synthesis of the natural product (+)‐paeonilactone B in enantiomerically pure form. In addition, preliminary experiments are described that illustrate a palladium‐catalysed variant proceeding by way of a π‐allyl intermediate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)